Top of the World - The Chicks It is hard to make me cry over a song especially but every time I hear it I do.
As a second choice: I Still Cry - Julie Miller There is a reference to September in the song and I connect it to 9/11 plus other losses when I hear it. The song was recorded far before 9/11.
Going through the John Prine album, you ask yourself how a kid in his twenties could write songs like he was writing. On an album with plenty of sad songs, "Hello in There" is the saddest. None of us are getting any younger. I heard Prine sing it just after he turned 70. I'm still having a hard time dealing with him being gone.
Taylor Swift - Ronan It’s the story of a young boy who was lost to cancer. The chorus ends on the lyric “you were my best four years.” I can’t listen to it.
The Beach Boys - When I Grow Up To Be A Man. When I hear it I think of what Brian still had to go through. Then there's the counting off of the years, which means more when you get older, and the "won't last forever" bit repeated at the end... I don't know if it's the saddest song I've ever heard, but (among others by Brian Wilson) it's definitely one of them.
Don't get sadder than this...a man who feels like a failure and just wants to end it all and ''go home" this demo version is gut wrenching
"Yes now you're gone, and from this moment on ... I'll be crying, crying, crying, cryyying, yeah Cryyying, CRYYYING, OOOO-VER YOUUUUU!"
"John and Linda live in Omaha / And Joe is somewhere on the road / We lost Davey in the Korean War / Still don't know what for /Don't matter anymore "
